


Between a Rock and a Perfectly Hard Place.

by Saltandburnboys



Category: Supernatural RPF
Genre: Blackmail, High school age - 18, Lap Sex, M/M, bottom!Jensen, cross-dressing, dub-con
Language: English
Status: Completed
Published: 2012-12-11
Updated: 2012-12-11
Packaged: 2017-11-20 21:01:45
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/589599
Author URL: https://archiveofourown.org/users/Saltandburnboys/pseuds/Saltandburnboys
Summary: <blockquote class="userstuff">
              <p>Jared couldn’t let such a great opportunity pass him by, right?</p>
            </blockquote>





	Between a Rock and a Perfectly Hard Place.

**Author's Note:**

> Disclaimer- Clearly this is an AU story; none of this ever happened. I do not own any of the actors in this story, especially not Jared or Jensen, they all belong to themselves. Jared and Jensen are not in a relationship, have never been and have no desire to be in a relationship; they are both happily married and not to each other which is awesome for both of them. No money was made from this story. 
> 
> Based on the spn-hardcore.livejournal.com ‘Virginity/First Time’ Meme prompt from last year:
> 
>  
> 
> Everyone at highschool knows Jensen, the captain of the football team. The boys want to be like him and the girls and even a few boys want to date him. And everybody knows that he is a kinky bastard who fucks everything with a heartbeat.
> 
> Jared is the captain of the debating club and...not so well known. He has a crush on Jensen since he first saw him but knows that he will never have a chance. It´s not that Jensen is mean to him, it´s simply that Jensen doesn´t know that Jared exists. And then Jared finds something out that changes everything. Somehow he discovers Jensen is still a virgin. 
> 
>  
> 
> Jared who over the years got more and more frustrated and thinks that Jensen is a tease uses this knowledge to blackmail Jensen in his house over the weekend while his parents are away. There the frustration and his pent-up sexual desire takes over. He forces Jensen to undress in front of him, forces him to wear panties and to stroke himself. The entire time he threats Jensen with exposure of his secret, his virginity.
> 
>  
> 
> What no one of them has expected is that Jensen gets off on the cross-dressing and Jared ordering him around. Things get out of control...
> 
>  
> 
> A/N: Never written cross-dressing before but I saw this and I just couldn’t resist (and virgin!Jensen is really my bread and butter so…). This was really fun to write; thanks for somersault_j and her post containing links to all the different memes – I was looking through the hardcore prompts from there and found this little gem. 
> 
>  
> 
> This is probably really crap because I wrote it at like three in the morning after doing a load of beta-ing and I’m not very good at writing porn at the best of times but…I’m just gonna post it anyway. I can always take it down again if you guys hate it!!! J
> 
>  
> 
> There is an abundant use of the words ‘Perfect’ and ‘Beautiful’ in this story – it’s a theme, alright, not just lazy writing! ;-P

** Between a Rock and a _Perfectly_ Hard Place. **

 

Jared hated him.  Jared _really_ hated him.

 

Jensen _Fucking_ Ackles, with his perfect face and his perfect body and his perfect fucking _everything_.  The guy had been only been at Jefferson High for six months, and already the entire student body (and half the faculty) worshipped the very ground he walked on.  While Jared, who’d been in this godforsaken place since he was twelve and had taken the school Debate Team to state every year he’d been Captain, was a fucking nobody. 

 

‘You know, you’d better hope the wind doesn’t change right now,’ Sandy said as she dropped down next to him, her lunch tray clattering loudly on the table, ‘So who are we glaring a…oh right, of _course_.’

 

‘I just don’t get it,’ Jared hissed, his voice full of venom, as he watched Danneel Harris, the Head Cheerleader and widely acknowledged hottest girl in school, climb onto Jensen’s lap, ‘He’s not _that_ hot and he’s not even that good at football; I bet he blew Coach Morgan to get Team Captain.  Everyone knows he’s a whore.’

 

Jared heard Sandy’s harsh inhale and struggled not to blush; that had been pretty low, even for him.  Not only _was_ Jensen a good football player and a great team Captain, Coach Morgan would never touch any of his boys like that – he was a straight shooter all the way and Jared knew that.  ‘Sorry,’ he muttered. 

 

But…it wasn’t entirely beyond the realm of possibility that Jensen _had_ blown some of the other teachers in the school because, cruel as it might be to say, Jensen was a slut.  The guy had never denied it, and while he never exactly bragged about his conquests like some of the guys on the squad, everybody seemed to know about it.  His torrid affair with his married 35 year old neighbour, the orgy on his class ski trip and the real reason he’d left his old school - getting caught with your pants around your ankles, bent over your headmaster’s desk, while he spanked you with a ruler apparently pissed some parents off…who knew - were all stories everyone had heard before Jensen had even gotten through his first day.

 

All of it added to Jensen’s ‘cool guy’ persona and the boy could have his pick of anyone in school.  It was weird; had Jensen not been so damn good looking, Jared was positive that he wouldn’t have been revered as some sort of Sex God; no, he would just have been labelled the whore that he was.  Jensen didn’t do girlfriends or boyfriends, hadn’t had one since he’d joined Jefferson High, but it was pretty common knowledge that the guy had slept with over half the school already.  Each _lucky_ student made sure that everybody knew about their night with Jensen Ackles.

 

Jared wasn’t sure who he hated more - Jensen with his perfect fucking everything or all those people who’d _had_ fucking perfect Jensen.

 

****

 

Well, that had gone a lot better than Jared had expected; he’d just met up with Coach Morgan to talk about him trying out for basketball Captain next year.  Jared had really shot up over the summer, clocking in at nearly 6 foot 5” now, and the extensive hours he’d spent at the gym had definitely started to pay off.  He knew that basketball Captain would look awesome on his college applications and he was eager to get in there before someone else snatched up the position. 

 

Jared was walking through the locker room on his way back from the field when he heard voices. 

 

‘I just don’t get it.  You pretty much own this school, you could have anyone you want and you’re not gonna take advantage of that?’

 

Jared didn’t recognise the guy’s voice; he was sure that he didn’t go to Jefferson High, so what the hell was he doing in their locker room?

 

‘God, Chris, would you just give it a rest?  I told you; I don’t just wanna fuck some random person so that I can say I’ve done it, I…I want it to be special, okay.’

 

No.  Fucking.  Way…

 

Jared’s mouth dropped open in shock because that had sounded an awful lot like Jensen Ackles but…but whoever had said that was _obviously_ a virgin and Jensen Ackles was no fucking virgin.

 

‘Awww, Jenny ain’t that sweet.’  The man let out a muffled laugh and Jared guessed that Jensen had just thrown a towel at him. 

 

‘Shut up, man.  You’re such an asshole; I don’t even know why we’re still friends.  Should’ve left you behind in Texas.’  Jensen grumbled as he slammed his locker shut.

 

Jared listened to them walk to the door as the other boy, Chris, chuckled, ‘Nah, you love me.  I’m like the big brother you never wanted.’ As soon as he heard the door open, Jared craned his neck around the side of the lockers to get a good look at the two guys because he _had_ to be sure.

 

And fuck! It _was_ Jensen.  Jensen Ackles was a fucking virgin and Jared was pretty sure that he didn’t want anyone to know about it.  Jared smiled, a plan forming in his mind, as he hitched his bag higher on his shoulder and made his way to the door.   _Perfect._

 

****

 

‘So, Jensen, that was a great game, you’re pretty damn fast,’ Jared drawled as he came round the lockers.  Jensen had nothing but a towel wrapped around his waist, and Jared let his eyes linger on the boy’s lightly muscled chest and broadening shoulders for a moment…God, he was pretty. 

 

Jensen looked up at him, a smile on his face, ‘Yeah?  Thanks, man.  Need to be fast or Coach’ll kick my ass.  Besides, I don’t think anyone was watching me today; Welling was on fire, right?’ 

 

Jared was a little thrown by that; he’d kind of expected Jensen to just nod and maybe make some asshole comment about how awesome he was, not talk about some other guy on the team.  He didn’t really know what to say so he just carried on with his original plan – it wasn’t that difficult, he’d been practising it for two days straight.  ‘Right.  Look, I just wanted to talk to you about something, maybe get your advice on it.’ 

 

Jensen frowned for a moment before he nodded, ‘What is it, Jared?’

 

Huh, maybe Jensen did know who Jared was after all.  ‘Well, there’s this guy I know and he’s, like, really popular and there’s all these rumours about him being some sort of sex fiend.’ Jensen’s frown deepened, ‘Only, I found out the other day that none of it’s true and he’s actually a fucking _virgin_.’  Jensen blanched and his frown was replaced by a look of abject horror, but that didn’t stop Jared; he was going to get what he wanted once and for all, ‘And I just don’t think it’s right, him lying to everyone, you know.  I think I should tell someone.  What do you think, Jen- _sen_?’

 

Jensen swallowed, sitting down shakily on the bench, ‘I don’t…what do…I…’

 

Jared took a seat next to him, his jacket brushing against Jensen’s bare arm, ‘Come to my house tonight, Jen, and we’ll see if you can convince me not to tell everyone what a phoney you are.’ 

 

Jared didn’t wait for an answer; he just got up and left the locker room, leaving Jensen alone on the bench.

 

There was no doubt in his mind that Jensen would come to his house that night.

 

****

 

Jared was so keyed up he didn’t know what to do with himself.  He was going to have Jensen Ackles _in_ his house, willing to do everything and anything he wanted.   And _God_ , how he wanted.

 

Jared jumped when the bell finally rang, and he forced himself to walk calmly to open the door.  Jensen stood on the doorstep, his eyes looking everywhere but at Jared, and Jared took a moment just to look over the boy in front of him; Jensen was wearing a loose pair of black jeans, a grey t-shirt, a plaid over-shirt, _and_ a bulky leather jacket.  Jared didn’t need a psychology degree to know that the boy was using the clothes as a shield, as an extra layer of protection against whatever Jared was going to make him do.  ‘Come on in, Jensen,’ Jared said, stepping back to let Jensen walk into the house. 

 

Jensen marched straight into the living room and turned to face Jared, his shoulders tense and his arms crossed, ‘Look, Jared, I don’t know what you’re playing at or what you want, but you should know that your GPA is higher than mine so getting me to do your homework probably isn’t gonna do you any favours.  And I don’t have any influence over who gets onto the football team, if that’s what you’re after, so…’

 

Jensen stood there awkwardly, obviously expecting Jared to send him on his way now, but poor, naive, _innocent_ Jensen clearly had no idea what Jared really wanted from him.  Things that had absolutely nothing to do with school. 

 

Jared crossed the room, aware of Jensen’s eyes following his every movement, and sat down on the couch.  It wasn’t until he was seated that he looked up at Jensen and said, ‘Strip.’  Jensen flinched at the order, and Jared watched the confusion cloud the boy’s face for a moment before he finally realised what Jared wanted.  Jensen paled, and he gaped at Jared like he couldn’t believe this was happening…but it was. 

 

Jared just waited, watching as Jensen weighed his options.  If he didn’t do what Jared said, Jared would out him to everyone, not only as a virgin but also as a liar – he’d look like a desperate loser and the rest of his high school career would be a nightmare.  He’d Hprobably lose his Captaincy of the football team as well, when none of the guys would work with him, and Jared knew that Jensen was relying on a football scholarship to get into Stanford.

 

Jared gave a mental cheer as he watched the resignation pass over Jensen’s too pretty face.  Jensen’s shaking hands reached up to his leather jacket and pushed it off his shoulders onto the floor. The over-shirt went next, and Jensen hesitated only for a second before pulling his t-shirt off too and letting it drop to the ground with the rest of his clothes.  The slowness, the nerves, the virginal flush rushing to Jensen’s cheeks made for the sexiest strip tease Jared had ever seen.  Even if Jensen hadn’t intended it to be. 

 

Jared let his knees fall open to make room for his rapidly swelling cock, as the boy’s trembling hands moved to the button of his jeans.  Jensen bit his lip and looked down at Jared, his eyes pleading, but Jared just directed his gaze to where Jensen’s hands rested on his jeans - the message clear.  Dropping his eyes to the floor again, Jensen unbuttoned his jeans and let them fall off his hips. 

 

The boxers went next.

 

Finally, Jensen stood in front of Jared in all his glory and it was, indeed, a sight to behold.  He’d caught glimpses of Jensen’s body in the locker room of course, but everyone knew that looking too long at other guys in the showers was just asking trouble.  Here, though…here, Jared could look for as long as he wanted.

 

Jensen was undeniably beautiful; Jared had never thought of a guy as beautiful before he’d met Jensen, but it was true.  The boy’s face was flawless - strong jaw, pale, unblemished skin, full plush mouth, high cheekbones and bright green eyes that burned right into Jared’s soul whenever the other boy looked at him.  And it wasn’t just his face.  Jensen’s body was nothing to be sniffed at either; the guy was tall, around six foot, and lean, with slim hips and a toned, washboard stomach.  And while that made Jensen taller and fitter than most of the guys at their school, it still meant he was more than a head shorter than Jared, and lacked the muscle definition Jared possessed.  Jared couldn’t help but think how small and vulnerable Jensen looked standing there, completely naked and hunched in on himself.  Jared almost wanted to laugh at the way the boy was using his hands to cover himself up; as if that would stop Jared from seeing what Jensen had hidden down there.

 

‘Let me see, Jensen.’  Jensen walked forward, not even offering the token protest that Jared had expected, and stopped in front of Jared.  Jared took hold of Jensen’s hands and the boy didn’t resist as he pushed them away, revealing the soft cock that had been hidden behind them.  Unsurprisingly, it was perfectly proportional, long and thick, but Jared felt a small tug of pride knowing that his was larger.  Jared released one of Jensen’s hands to reach behind the pillow next to him and pull out his present – he’d bought them especially for Jensen. 

 

Jensen’s eyes widened when Jared pushed the panties into his hands, but Jared didn’t miss the way the boy’s cock twitched, hardening slightly, as his fingers touched the satin.  _Interesting_.  ‘Jared…I don’t…?’

 

‘Put them on, Jenny,’ Jared ordered as he relaxed back into the couch, resting his arms along the back.  Jensen just stood there, staring at the frilly, pink panties in his hands. ‘Or I could just ring up Tom and tell him all about that interesting conversation I overheard in…’

 

Jensen pulled on the panties so fast that he almost fell over in his haste to get them on.  And fucking hell…Jared had never thought he’d be into something like this; he’d bought the panties to humiliate Jensen more than anything else, but _damn_ did they look fucking sexy on the guy.  The flush on Jensen’s cheeks darkened as he stood with his arms folded across his chest, his eyes avoiding Jared’s completely. 

 

And Jared could see why; little Jenny was half hard in his panties, his cock already tenting the satin slightly.  So maybe Jared wasn’t the only one getting off on Jensen wearing them. 

 

‘You like those, baby?’ Jared asked, his voice rough and low in a way he’d never heard it before.  ‘Why don’t you put your hand down there, play with that little cock of yours?’

 

Jared nearly came in his pants when Jensen immediately followed the order, the boy dipping his hand into the panties and gripping his cock.  ‘No, play with it _over_ the panties, Jen; wanna see you get them all wet and sticky.’  Jensen pulled his hand out of the panties and gripped his dick through the silky material just like Jared had told him to.  As he worked his hand over his hardening shaft, Jensen’s head fell back, exposing the long line of his throat to Jared.  _Christ_ , Jared wanted nothing more than to walk right over there and lick a strip up that perfect neck, kiss his way along Jensen’s jaw, pull the boy’s ear lobe into his mouth and suck on it until Jensen came. 

 

But he was enjoying this game too much for that; he liked giving Jensen orders, and he liked watching the other boy follow them even more.  Jensen was still fondling himself through the panties when Jared managed to drag his eyes away from the boy’s neck, and Jared could tell the boy was close to shooting his load.  ‘Come here, Jensen.’  It took a moment for Jensen to react to Jared’s words, obviously too lost in chasing his own pleasure, but after a few moments, the boy’s hand stilled.  It didn’t move away, though, just stayed cupping his hard cock through the flimsy material.  ‘Come here.’  Jared repeated and, just like before, Jensen immediately made his way over to Jared.  Jared pulled his knees together and patted his knee, ‘Hop on, baby.’

 

Jared saw something flash in Jensen’s eyes and he thought that maybe Jensen had finally reached his limit and was going to refuse; he was pleasantly surprised, therefore, when the boy climbed into his lap, without any further prompting, and settled on his thighs.  His hand still cradling his cock.  Jared reached forwards and grabbed both of Jensen’s hands and placed them on his own shoulders. 

 

‘You know, Jen, I’m starting to think that you like me telling you what to do.  Is that true, baby?’  Jensen squirmed on Jared’s lap, his breath coming in short, hard pants, ‘Do you like giving up control to me, Jen?’ He reached up and grabbed Jensen by the back of the neck, pulling the boy down until his ear was barely an inch from Jared’s lips,  ‘Do you like the fact that I’m bigger and stronger than you, that I could hold you down and fuck you so hard you’d be leaking my come for days.’  Jensen jerked in his hold and for a second Jared thought that the boy was pulling away from him, but then he felt Jensen’s come splash on his shirt. 

 

Jensen slumped forwards, his face buried in Jared’s neck, his breath warm against Jared’s skin.  _Fuck_ , that was hot.  Jared was hard enough to cut glass and he still had a pliant, beautiful Jensen in his arms.  Jared tucked his hand between them and ran his fingers through the come on Jensen’s stomach, coating them completely, before reaching round behind Jensen.  He carefully used his other hand to pull the panties aside before touching his come covered index finger to Jensen’s virgin hole.

 

Jensen flinched at the touch, his body arching away from Jared’s finger, but Jared just turned his head, pressed a kiss to Jensen’s temple and whispered, ‘shhh,’ as he pushed his finger inside.  It was hot, _scorching_ , and so fucking tight that Jared felt dizzy at the mere thought of how it would feel around his dick.  Unlike Jensen, Jared wasn’t a virgin, he’d screwed a couple of girls from their year but none of them had been as tight as Jensen. 

 

He pushed his finger in a little further, stopping when he felt Jensen clench down.  ‘Relax, baby,’ he murmured against Jensen’s skin and the boy did, following Jared’s orders so prettily, so perfectly.  It wasn’t long before Jared had three fingers in Jensen’s hole, the slick noise of him pumping them in and out adding to soft, little gasps Jensen made every time Jared’s fingers grazed his prostate.  Jensen was hard again, the head of his cock peeking out from the top of the panties, his body grinding down unconsciously on Jared’s fingers.  And Jared couldn’t wait any longer; three fingers would just have to be enough because if Jared didn’t get inside Jensen soon, then he was gonna blow his load before they’d even gotten to the actual fucking.  And that was so not happening.     

 

The little, choked off whimper Jensen made when Jared pulled out his fingers was almost enough to have Jared shooting but he quickly clamped a hand down on his cock to stop himself.  Once he was sure he had himself back under control, Jared let go and raised his hand to Jensen’s face, tilting the other boy’s head up and looking into his eyes.  Jensen looked a little dazed, his pupils blown wide with lust and his lips swollen and red and Jared was pretty sure he’d never seen anything more beautiful in his whole life.  He was starting to think that one time with Jensen was just not going to be enough…hell, a hundred times with Jensen probably wouldn’t be enough to slake his lust for the other boy.  ‘You okay, baby?’ Jared asked, his thumb rubbing tenderly over Jensen’s jaw and he was surprised that he actually meant it; he needed to know that Jensen was alright. 

 

Instead of replying, Jensen swooped down and caught Jared’s lips in a kiss, and that was all the answer Jared needed.  Letting his hand wander to the back of Jensen’s head, Jared held him in place as he pushed his tongue into the boy’s mouth, licking possessively inside.  Jared let his tongue play against Jensen’s as he reached back round Jensen and drew the panties aside again.

 

Jensen pulled back immediately, looking a little more lucid now that Jared wasn’t inside him and a lot more scared as his lubed hole was exposed, and Jared didn’t hesitate before pushing his finger back in as a distraction.  Jensen’s eyes fluttered closed, his mouth going slack, as Jared worked his finger in and out of Jensen’s hole again, ‘That feels good doesn’t it, baby?’  He pressed a finger into Jensen’s prostate and the boy let out a deep, guttural moan that sent a thrill of heat through Jared’s body, ‘Gonna feel even better in a minute.’  Jared used his other hand to grasp Jensen’s hip and guide the boy onto his knees; Jensen went without complaint, clearly too distracted by what Jared was doing in his ass to figure out where Jared was taking this. 

 

Before Jensen could catch on, Jared withdrew his finger and pulled Jensen down onto his cock.  Jensen cried out, his hands tightening almost painfully on Jared’s shoulders as his eyes flew open.  That had probably hurt; Jensen was incredibly tight and Jared was more than proportional in size, but Jared was pleased to see that the other boy was still hard, his cheeks flushed with arousal and his plush bottom lip caught between his teeth as he stared down at Jared. 

 

And if Jared had thought Jensen was perfect before, it was nothing compared to how perfect he looked sat on Jared’s lap, hard and weeping in a pair of satin panties while his ass fit snugly around Jared’s cock.  Jared’s thumbs stroked soothing circles into Jensen’s hip bones.  ‘Now, Jen, you’re gonna lift yourself up,’ he pushed gently at Jensen’s hips so the boy would understand what he was staying, ‘then drop yourself back down.  You understand?’  Jensen stared at him for a moment before nodding. 

 

Jensen’s thighs shook as he raised himself up, the slow drag against Jared’s cock the best kind of tease, and let out a long, dirty moan as he dropped himself back down.  Jensen had barely settled on Jared’s thighs before he was lifting himself up again, his eyes now closed, and dropping back down.  Jared watched in near awe as Jensen picked up the pace, sliding up and down Jared’s cock like he was made for it, and all too soon Jared felt his orgasm building at the bottom of his spine.  ‘Come on, ride me, baby, ride me,’ he urged, gripping Jensen’s hips and pushing him to go faster. 

 

And Jensen did.  Taking one hand off Jared’s shoulder, Jensen placed it on the arm of the sofa as he changed the angle of his body slightly and rode Jared even harder.  If the litany of breathy ‘Oh God’s and curses that spewed from Jensen mouth was anything to go by, the new position was working for him as well as it was working for Jared.

 

It wasn’t until Jared was on the very verge of coming that he pulled Jensen again and whispered in his ear, ‘Come for me.’  Jensen screamed, his cry muffled by Jared’s neck, as he coated both their stomachs and the panties in come for the second time that night.  Jared let out a curse of his own as Jensen’s ass tightened around his cock, pushing him over the edge into probably the hardest orgasm he’d ever had. 

 

Once Jared had gotten his breath back and was able to think clearly again, he brought his arms up around Jensen’s shoulders and pulled the other boy against his body.  It wasn’t until Jared spoke that he realised that Jensen had passed out and was sleeping against his chest.  He couldn’t help but smile as he lifted the boy off his cock and lay him down on the sofa.  Jared quickly ran to the bathroom, grabbed a washcloth, and wandered back to wipe himself and Jensen down.    

 

He stared at the soiled panties encasing Jensen’s now soft cock.  He bit his lip, completely torn as to what to do next, before reaching a decision and walking over to his school bag.  He grabbed what he needed and strode back over to the couch before slowly taking the come covered pink panties off Jensen and sliding a pair of black lacy ones on in their place. 

 

Heck, he had all night, right?  Jensen must have known that when he’d come to Jared’s house, even if he hadn’t known what Jared had intended to do with the time.  Besides, Jared was pretty sure Jensen wasn’t going to be all that opposed to a couple more rounds.  Jared had a _whole_ backpack full of panties he’d bought specially for Jensen, and maybe next time he’d even let Jensen choose which pair he wanted to wear.  He glanced down at the naked boy lying unconscious on his couch, revelling in the thrill of power that ran through him at the sight…maybe not. 

 

 

Thanks for reading; hope you guys enjoyed it!! J

 

xx

  
 


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